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Direct catalytic enantio- and diastereoselective ketone aldol reactions of isocyanoacetates.

ABSTRACT: A catalytic asymmetric aldol addition/cyclization reaction of unactivated ketones with isocyanoacetate pronucleophiles has been developed. A quinine-derived aminophosphine precatalyst and silver oxide were found to be an effective binary catalyst system and promoted the reaction to afford chiral oxazolines possessing a fully substituted stereocenter with good diastereoselectivities and excellent enantioselectivities.

SUBMITTER: de la Campa R 

PROVIDER: S-EPMC4678506 | biostudies-literature | 2015 Apr

REPOSITORIES: biostudies-literature

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Direct catalytic enantio- and diastereoselective ketone aldol reactions of isocyanoacetates.

de la Campa Raquel R   Ortín Irene I   Dixon Darren J DJ  

Angewandte Chemie (International ed. in English) 20150303 16

A catalytic asymmetric aldol addition/cyclization reaction of unactivated ketones with isocyanoacetate pronucleophiles has been developed. A quinine-derived aminophosphine precatalyst and silver oxide were found to be an effective binary catalyst system and promoted the reaction to afford chiral oxazolines possessing a fully substituted stereocenter with good diastereoselectivities and excellent enantioselectivities. ...[more]

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